Palladium-catalyzed enantioselective allylic alkylation of trifluoromethyl group substituted racemic and acyclic unsymmetrical 1,3-disubstituted allylic esters with malonate anions.

Journal: Organic & Biomolecular Chemistry
Published:
Abstract

We examined the palladium-catalyzed allylic alkylation of trifluoromethyl group-substituted racemic and acyclic unsymmetrical 1,3-disubstituted allylic benzoate with a malonate anion, and succeeded in obtaining an enantiomerically enriched product in high yields with high ee values through the dynamic kinetic asymmetric transformation (DYKAT). The best result was attained by the [Pd(C3H5)(cod)]BF4/(S)-tol-BINAP in the presence of BSA or DMAP as a base.

Authors
Kazunori Ikeda, Takashi Futamura, Taisyun Hanakawa, Maki Minakawa, Motoi Kawatsura